Asymmetric Friedel-Crafts alkylation of pyrrole with nitroalkenes catalyzed by a copper complex of a bisphenol A-derived Schiff base

OZDEMIR H. S., Sahin E., ÇAKICI M., KILIÇ H.

TETRAHEDRON, vol.71, no.19, pp.2882-2890, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 71 Issue: 19
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tet.2015.03.059
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2882-2890
  • Keywords: Chiral copper complex, Pyrrole, Nitroalkene, Asymmetric Friedel-Crafts alkylation, Asymmetric synthesis, INDOLES, ENONES
  • Ataturk University Affiliated: Yes

Abstract

The asymmetric Friedel-Crafts (FC) alkylation of pyrrole with nitroalkenes was mediated by CuBr2 and a novel bisphenol A-derived chiral catalyst at room temperature. The catalyst was found to be applicable for the asymmetric FC alkylation of pyrrole with a wide range of nitroalkenes, affording optically active alkylated pyrroles with enantioselectivities up to 94%. Furthermore, enantiomerically pure 3-nitro-2-arylpropanamides were prepared by the oxidative cleavage of the pyrrole rings in the FC products with NaIO4/RuCl3 to demonstrate the synthetic application of the products. (C) 2015 Elsevier Ltd. All rights reserved.